Dichloromethane → O2-benzyl O9-tert-butyl 2,9-diazaspiro[5.5]undecane-2,9-dicarboxylate

HRID 2284871Notes

Reaction equation

HRID 2284871 reaction equation
Cl.[CH2:2]1[C:7]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:6][NH:5][CH2:4][CH2:3]1.ClCCl.C(N(CC)CC)C.Cl[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>O>[CH2:2]1[C:7]2([CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[CH2:6][N:5]([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 71464197Tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride

Product 1

HCID 118049948O2-benzyl O9-tert-butyl 2,9-diazaspiro[5.5]undecane-2,9-dicarboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 20 L temperature controlled reactor charge tert-butyl 4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (2.06 moles; 600.00 g) followed by dichloromethane (6.00 L), then triethylamine (4.33 moles; 604 mL) is added. Set the jacket of the reactor to 0° C. When the temperature of the reaction mixture reaches 5° C., add benzyl chloroformate (2.10 moles; 311 mL) over about 20 minutes keeping the internal temperature below 20° C. When the addition is complete, warm the jacket to room temperature and stir the mixture overnight. Pour the reaction mixture into water (4 L) and separate the mixture. Concentrate the organics under reduced pressure to give the title compound (838 g; assumed 95.65% purity and 100% yield for the purposes of calculation in the next reaction) mass spectrum (m/z): 411.2 (M+23).

Workup

  1. customto 0° C
  2. customreaches 5° C.
  3. customthe internal temperature below 20° C
  4. additionWhen the addition
  5. customseparate the mixture
  6. concentrationConcentrate the organics under reduced pressure

Sources & evidence

ORD record
ord-9799e32c2a3048f4804da459b1d876e0
Source dataset
uspto-grants-2015_09
Patent number
US09145437B2

Reaction notes

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